The podcast is devoted to the musical Wicked and specifically to the actresses in the leading roles of Elphaba and Glinda.
The title of the podcast comes from the song "Sentimental Man" in Act I of Wicked, which the hosts admit they would often skip when listening to the cast album.
Most episodes include some of the same standard questions for the guest: As of 2024, Bianchi and Brown have interviewd nearly all the actresses who portrayed Elphaba on Broadway.
In October 2022, Theatrely, a Broadway news outlet, announced that Sentimental Men would be hosted on their platform.
[3] In October 2023, for the 20th anniversary of Wicked, Bianchi and Brown moderated a panel about the musical at New York Comic Con.